Fe(III)-catalyzed stereoselective synthesis of deoxyglycosides using stable bifunctional deoxy-phenylpropiolate glycoside donors

Anjali Aghi; Sankar Sau; Amit Kumar

doi:10.1016/j.carres.2024.109051

Fe(III)-catalyzed stereoselective synthesis of deoxyglycosides using stable bifunctional deoxy-phenylpropiolate glycoside donors

Carbohydr Res. 2024 Feb:536:109051. doi: 10.1016/j.carres.2024.109051. Epub 2024 Feb 2.

Authors

Anjali Aghi¹, Sankar Sau¹, Amit Kumar²

Affiliations

¹ Department of Chemistry, Indian Institute of Technology Patna, Bihta, Bihar, 801106, India.
² Department of Chemistry, Indian Institute of Technology Patna, Bihta, Bihar, 801106, India. Electronic address: [email protected].

PMID: 38325069
DOI: 10.1016/j.carres.2024.109051

Abstract

Herein, we report a mild and economical route for the stereoselective synthesis of 2-deoxy and 2,6-dideoxyglycosides via FeCl₃-catalyzed activation of bench stable deoxy-phenylpropiolate glycosyl donors (D-PPGs). Optimized reaction conditions work well under additive-free conditions to afford the corresponding 2-deoxy and 2,6-dideoxyglycosides in good yields with high α-anomeric selectivity by reacting with sugar and non-sugar-based acceptors. The optimized conditions were also extended for disarmed D-PPG donors. In addition, the developed strategy is amenable to high-scale-up synthesis.

Keywords: Additive-free glycosylation; Bifunctional donors; Deoxyglycosides; Stereoselective.

MeSH terms

Carbohydrates
Catalysis
Ferric Compounds*
Glycosides*
Glycosylation
Stereoisomerism

Substances

Glycosides
Ferric Compounds
Carbohydrates